Binap-silver-catalyzed enantioselective multicomponent 1,3-dipolar cycloaddition of azomethines ylides derived from ethyl glyoxylate

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Title: Binap-silver-catalyzed enantioselective multicomponent 1,3-dipolar cycloaddition of azomethines ylides derived from ethyl glyoxylate
Authors: Mancebo Aracil, Juan | Nájera, Carmen | Sansano, Jose M.
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Enantioselective | Cycloaddition
Knowledge Area: Química orgánica
Issue Date: 15-Jul-2015
Publisher: Elsevier
Citation: Tetrahedron: Asymmetry. 2015, 26(12-13): 674-678. doi:10.1016/j.tetasy.2015.05.005
Abstract: The enantioselective binap–silver catalyzed multicomponent 1,3-dipolar cycloaddition using ethyl glyoxylate, phenylalanine ethyl ester, and maleimides is described. The employment of basic silver carbonate allows the reaction to take place in the absence of an extra base giving high yields and ee. In addition, low-level calculations regarding the importance of the benzyl substituent at the α-position of the amino ester justify the expected absolute configuration of the final cycloadducts and the observed high enantiodiscrimination.
Sponsor: Financial support was provided by the Spanish Ministerio de Ciencia e Innovación (MICINN) (projects CTQ2010-20387, and Consolider Ingenio 2010, CSD2007-00006), the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P, and CTQ2014-51912-REDC), FEDER, the Generalitat Valenciana (PROMETEO 2009/039 and PROMETEOII/2014/017), and the University of Alicante.
ISSN: 0957-4166 (Print) | 1362-511X (Online)
DOI: 10.1016/j.tetasy.2015.05.005
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2015 Elsevier Ltd.
Peer Review: si
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